Milk thistle (Silybum marianum L.) seeds are known for their high amounts of bioactive silymarin complex and oil, both contributing to its potential as a functional food. This study aimed to evaluate the phytochemical composition of four milk thistle varieties (Silma, Silyb, Mirel, and Moravia 55), focusing on the silymarin complex, oil yield, and fatty acid profile. Silymarin content was quantified by high-performance liquid chromatography with diode-array detection (HPLC-DAD) following ultrasound-assisted extraction (USE). Pressurized liquid extraction (PLE) was employed for determining oil yield, and the fatty acid composition was performed by gas chromatography with flame ionization detection (GC-FID). Results showed significant variability between genotypes. The total silymarin content ranged from 12.69 to 20.28 mg·g⁻¹ DW, with silychristin, silybin A, and silybin B as major constituents. Oil content varied from 22.81 to 26.25%, with Mirel 2 showing the highest yield. Fatty acid analysis revealed a high proportion of unsaturated fatty acids (79.30-83.30%), with linoleic (53.53-62.27%) and oleic (20.17-24.57%) acids being the most abundant. The results were further evaluated by Principal Component Analysis and hierarchical cluster analysis. The study's findings may contribute to the strategic selection of milk thistle genotypes for pharmaceutical or nutritional applications, and support targeted cultivation to optimize phytochemical content.
- Klíčová slova
- Silybum marianum L., Fatty acids, Oil, Silymarin complex,
- MeSH
- funkční potraviny analýza MeSH
- genotyp MeSH
- mastné kyseliny * analýza MeSH
- nenasycené mastné kyseliny analýza MeSH
- oleje rostlin * analýza chemie MeSH
- ostropestřec mariánský * chemie genetika MeSH
- semena rostlinná chemie genetika MeSH
- silibinin MeSH
- silymarin * analýza MeSH
- vysokoúčinná kapalinová chromatografie MeSH
- Publikační typ
- časopisecké články MeSH
- Názvy látek
- mastné kyseliny * MeSH
- nenasycené mastné kyseliny MeSH
- oleje rostlin * MeSH
- silibinin MeSH
- silychristin MeSH Prohlížeč
- silymarin * MeSH
BACKGROUND: Over the past two decades, the global incidence of gout has markedly increased, affecting people worldwide. Considering the side effects of xanthine oxidase (XO) inhibitor drugs (e.g. allopurinol and febuxostat) used in the treatment of hyperuricemia and gout, the potential application of phytochemicals has been widely studied. In addition, XO also takes part in the elimination of certain drugs, including 6-mercaptopurine. In the current explorative study, we aimed to examine the potential effects of tea catechins, resveratrol, silymarin flavonolignans and some of their conjugated metabolites on XO-catalyzed xanthine and 6-mercaptopurine oxidation, applying in vitro assays and modeling studies. RESULTS: Catechins, resveratrol and resveratrol conjugates exerted no or only weak inhibitory effects on XO. Silybin A, silybin B and isosilybin A were weak, silychristin was a moderate, while 2,3-dehydrosilychristin was a potent inhibitor of the enzyme. Sulfate metabolites of silybin A, silybin B and isosilybin A were considerably stronger inhibitors compared to the parent flavonolignans, and the sulfation of 2,3-dehydrosilychristin slightly increased its inhibitory potency. Silychristin was the sole flavonolignan tested, where sulfate conjugation decreased its inhibitory effect. CONCLUSION: 2,3-Dehydrosilychristin seems to be a promising candidate for examining its in vivo antihyperuricemic effects, because both the parent compound and its sulfate conjugate are highly potent inhibitors of XO. © 2024 The Author(s). Journal of the Science of Food and Agriculture published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.
- Klíčová slova
- catechins, enzyme inhibition, resveratrol, silymarin, sulfate conjugates, xanthine oxidase,
- MeSH
- inhibitory enzymů chemie MeSH
- katalýza MeSH
- katechin * chemie MeSH
- lidé MeSH
- merkaptopurin * chemie metabolismus MeSH
- oxidace-redukce MeSH
- resveratrol * chemie MeSH
- silibinin chemie MeSH
- silymarin * chemie MeSH
- xanthin * chemie metabolismus MeSH
- xanthinoxidasa * chemie metabolismus antagonisté a inhibitory MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- Názvy látek
- inhibitory enzymů MeSH
- katechin * MeSH
- merkaptopurin * MeSH
- resveratrol * MeSH
- silibinin MeSH
- silymarin * MeSH
- xanthin * MeSH
- xanthinoxidasa * MeSH
Silymarin is an extract obtained from the seeds of milk thistle (Sylibum marianum L., Asteraceae) and contains several structurally related flavonolignans and a small family of flavonoids. Mouse spleen cells represent highly sensitive primary cells suitable for studying the pharmacological potential and biofunctional properties of natural substances. Cultivation of splenocytes for 24 h under standard culture conditions (humidity, 37 °C, 5% CO2, atmospheric oxygen) resulted in decreased viability of splenocytes compared to intact cells. A cytoprotective effect of silybin (SB), silychristin (SCH) and 2,3-dehydrosilybin (DHSB) was observed at concentrations as low as 5 µmol/ml. At 50 µmol/ml, these substances restored and/or stimulated viability and mitochondrial membrane potential and had anti-apoptotic effect in the order SB > DHSB > SCH. The substances demonstrated a concentration-dependent activity in restoring the redox balance based on the changes in the concentration of reactive oxygen species (ROS), hydrogen peroxide (H2O2) and nitric oxide. This was in the order DHSB > SCH > SB, which correlated with the suppressed expression of nuclear factor erythroid 2-related factor 2 (Nrf2), catalase and glutathione peroxidase. The strong stimulation of the superoxide dismutase 1 gene converting ROS to H2O2 points to its dominant role in the maintaining redox homeostasis in splenocytes, which was disrupted by oxidative stress due to non-physiological culture conditions. Our study showed significant differences in the cytoprotective, antioxidant and anti-apoptotic activities of SB, SCH, and DHSB on splenocytes exposed to mild and AAPH-induced oxidative stress.
- Klíčová slova
- 2,3-dehydrosilybin, Apoptosis, Mouse splenocytes, Redox balance, Silybin, Silychristin, Viability,
- MeSH
- antioxidancia * farmakologie MeSH
- apoptóza * účinky léků MeSH
- cytoprotekce * účinky léků MeSH
- faktor 2 související s NF-E2 metabolismus MeSH
- membránový potenciál mitochondrií účinky léků MeSH
- myši inbrední BALB C MeSH
- myši MeSH
- oxid dusnatý metabolismus MeSH
- oxidační stres účinky léků MeSH
- peroxid vodíku metabolismus MeSH
- reaktivní formy kyslíku metabolismus MeSH
- silibinin MeSH
- silymarin * farmakologie analogy a deriváty MeSH
- slezina * cytologie účinky léků metabolismus MeSH
- viabilita buněk účinky léků MeSH
- zvířata MeSH
- Check Tag
- myši MeSH
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- Názvy látek
- antioxidancia * MeSH
- dehydrosilybin MeSH Prohlížeč
- faktor 2 související s NF-E2 MeSH
- oxid dusnatý MeSH
- peroxid vodíku MeSH
- reaktivní formy kyslíku MeSH
- silibinin MeSH
- silychristin MeSH Prohlížeč
- silymarin * MeSH
SCOPE: This multi-omic study investigates the bidirectional interactions between gut microbiota and silymarin metabolism, highlighting the differential effects across various age groups. Silymarin, the extract from Silybum marianum (milk thistle), is commonly used for its hepatoprotective effects. METHODS AND RESULTS: An in vitro fermentation colon model was used with microbiota from 20 stool samples obtained from healthy donors divided into two age groups. A combination of three analytical advanced techniques, namely proton nuclear magnetic resonance (1H NMR), next-generation sequencing (NGS), and liquid chromatography-mass spectrometry (LC-MS) was used to determine silymarin microbial metabolites over 24 h, overall metabolome, and microbiota composition. Silymarin at a low diet-relevant dose of 50 µg mL-1 significantly altered gut microbiota metabolism, reducing short-chain fatty acid (acetate, butyrate, propionate) production, glucose utilization, and increasing alpha-diversity. Notably, the study reveals age-related differences in silymarin catabolism. Healthy elderly donors (70-80 years) exhibited a significant increase in a specific catabolite associated with Oscillibacter sp., whereas healthy young donors (12-45 years) showed a faster breakdown of silymarin components, particularly isosilybin B, which is associated with higher abundance of Faecalibacterium and Erysipelotrichaceae UCG-003. CONCLUSION: This study provides insights into microbiome functionality in metabolizing dietary flavonolignans, highlighting implications for age-specific nutritional strategies, and advancing our understanding of dietary (poly)phenol metabolism.
- Klíčová slova
- age‐related differences, gut microbiota, multi‐Omics analysis, polyphenols, silymarin metabolism,
- MeSH
- dítě MeSH
- dospělí MeSH
- feces mikrobiologie MeSH
- fermentace MeSH
- kolon * mikrobiologie metabolismus účinky léků MeSH
- kyseliny mastné těkavé metabolismus MeSH
- lidé středního věku MeSH
- lidé MeSH
- mladiství MeSH
- mladý dospělý MeSH
- senioři nad 80 let MeSH
- senioři MeSH
- silymarin * farmakologie MeSH
- střevní mikroflóra * účinky léků fyziologie MeSH
- zdraví dobrovolníci pro lékařské studie MeSH
- Check Tag
- dítě MeSH
- dospělí MeSH
- lidé středního věku MeSH
- lidé MeSH
- mladiství MeSH
- mladý dospělý MeSH
- mužské pohlaví MeSH
- senioři nad 80 let MeSH
- senioři MeSH
- ženské pohlaví MeSH
- Publikační typ
- časopisecké články MeSH
- Názvy látek
- kyseliny mastné těkavé MeSH
- silymarin * MeSH
Restoring the structures and functions of tissues along with organs in human bodies is a topic gathering attention nowadays. These issues are widely discussed in the context of regenerative medicine. Excipients/delivery systems play a key role in this topic, guaranteeing a positive impact on the effectiveness of the drugs or therapeutic substances supplied. Advances in materials engineering, particularly in the development of hydrogel biomaterials, have influenced the idea of creating an innovative material that could serve as a carrier for active substances while ensuring biocompatibility and meeting all the stringent requirements imposed on medical materials. This work presents the preparation of a natural polymeric material based on pullulan modified with silymarin, which belongs to the group of flavonoids and derives from a plant called Silybum marianum. Under UV light, matrices with a previously prepared composition were crosslinked. Before proceeding to the next stage of the research, the purity of the composition of the matrices was checked using Fourier-transform infrared (FT-IR) spectroscopy. Incubation tests lasting 19 days were carried out using incubation fluids such as simulated body fluid (SBF), Ringer's solution, and artificial saliva. Changes in pH, electrolytic conductivity, and weight were observed and then used to determine the sorption capacity. During incubation, SBF proved to be the most stable fluid, with a pH level of 7.6-7.8. Sorption tests showed a high sorption capacity of samples incubated in both Ringer's solution and artificial saliva (approximately 350%) and SBF (approximately 300%). After incubation, the surface morphology was analyzed using an optical microscope for samples demonstrating the greatest changes over time. The active substance, silymarin, was released using a water bath, and then the antioxidant capacity was determined using the Folin-Ciocâlteu test. The tests carried out proved that the material produced is active and harmless, which was shown by the incubation analysis. The continuous release of the active ingredient increases the biological value of the biomaterial. The material requires further research, including a more detailed assessment of its balance; however, it demonstrates promising potential for further experiments.
- Klíčová slova
- flavonoids, polyethylene glycol, polymers, pullulan, silymarin,
- MeSH
- glukany * chemie MeSH
- koncentrace vodíkových iontů MeSH
- lékové transportní systémy metody MeSH
- lidé MeSH
- nosiče léků * chemie MeSH
- polyethylenglykoly * chemie MeSH
- silymarin * chemie MeSH
- spektroskopie infračervená s Fourierovou transformací MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- Názvy látek
- glukany * MeSH
- nosiče léků * MeSH
- polyethylenglykoly * MeSH
- pullulan MeSH Prohlížeč
- silymarin * MeSH
Plant foods are receiving increasing attention as a valuable source of health beneficial compounds. Understanding the impact of growing conditions on the quality of milk thistle is critical for determining appropriate agro-ecological and agro-economic parameters for its production and, subsequently, food products rich in health-beneficial compounds. For this purpose, a randomized milk thistle cultivation trial was established in the experimental field of Agritec Plant Research Plc. in Šumperk, Czech Republic, and carried out for two subsequent growing seasons in 2020 and 2021. The milk thistle achenes, variety Mirel, were sown in the row width of 12.5, 25 and 37 cm; and the qualitative parameters of each field trial such as achenes yields, silymarin complex determination and also antioxidant assessment (total phenolic content, total flavonoids content, DPPH and ABTS radical scavenging activity) were evaluated. The environmental impact of the extraction process was reduced by using pressurized liquid extraction with 60% EtOH (v/v). The weather conditions during the trial as well as the row spacing of milk thistle sowing were revealed to have a significant influence on the evaluated parameters (p ≤ 0.05). The highest yields of evaluated parameters were obtained for the growing season 2021 and the row spacing of 37 cm.
- Klíčová slova
- Antioxidant assessment, Row width, Silybum marianum L., Silymarin complex,
- MeSH
- antioxidancia farmakologie analýza MeSH
- flavonoidy analýza MeSH
- ostropestřec mariánský chemie MeSH
- semena rostlinná chemie MeSH
- silymarin * farmakologie analýza chemie MeSH
- Publikační typ
- časopisecké články MeSH
- Názvy látek
- antioxidancia MeSH
- flavonoidy MeSH
- silymarin * MeSH
Metabolic syndrome is diagnosed mainly in people of economically developed parts of the world and it affects 20-25% of the adult population worldwide. Nowadays, it is also more frequently diagnosed in children and adolescents. In addition to standard treatment that often involves polypharmacotherapy, and thus increases risk of side effects caused by drugdrug interactions, it is appropriate to look for alternative tools to support the treatment of metabolic syndrome components. Natural polyphenolic compounds, usually present in the so-called functional foods, are suitable candidates for that matter, due to the bioactivity and beneficial effects on the human body. Quercetin, troxerutin, diosmin, hesperidin or silybin are among the currently studied and used natural polyphenolic compounds with a positive effect on aspects of the metabolic syndrome. In addition to their antioxidant and anti-inflammatory effects, these compounds have other positive properties that very often outweigh their side effects whilst their usage in the pharmacotherapy.
- Klíčová slova
- NAFLD, diosmin, metabolic syndrome, polyphenolic compounds, quercetin, silymarin, troxerutin,
- MeSH
- antiflogistika MeSH
- antioxidancia škodlivé účinky MeSH
- diosmin * terapeutické užití MeSH
- dítě MeSH
- dospělí MeSH
- hesperidin * terapeutické užití MeSH
- lidé MeSH
- metabolický syndrom * farmakoterapie MeSH
- mladiství MeSH
- quercetin MeSH
- silibinin terapeutické užití MeSH
- Check Tag
- dítě MeSH
- dospělí MeSH
- lidé MeSH
- mladiství MeSH
- Publikační typ
- časopisecké články MeSH
- Názvy látek
- antiflogistika MeSH
- antioxidancia MeSH
- diosmin * MeSH
- hesperidin * MeSH
- quercetin MeSH
- silibinin MeSH
Covering: 2015 up to 2022 (Feb)Silymarin, an extract of milk thistle (Silybum marianum) fruits, has been used in various medicinal applications since ancient times. A major component of silymarin is the flavonolignan silybin and its relatives isosilybin, silychristin, silydianin, 2,3-dehydrosilybin, and some others. Except for silydianin, they occur in nature as two stereomers. This review focuses on recent developments in chemistry, biosynthesis, modern advanced analytical methods, and transformations of flavonolignans specifically reflecting their chirality. Recently described chemotypes of S. marianum, but also the newest findings regarding the pharmacokinetics, hepatoprotective, antiviral, neuroprotective, and cardioprotective activity, modulation of endocrine functions, modulation of multidrug resistance, and safety of flavonolignans are discussed. A growing number of studies show that the respective diastereomers of flavonolignans have significantly different activities in anisotropic biological systems. Moreover, it is now clear that flavonolignans do not act as antioxidants in vivo, but as specific ligands of biological targets and therefore their chirality is crucial. Many controversies often arise, mainly due to the non-standard composition of this phytopreparation, the use of various undefined mixtures, the misattribution of silymarin vs. silybin, and also the failure to consider the chemistry of the respective components of silymarin.
Milk thistle (Silybum marianum) provides several possible benefits for horses, namely anti-inflammatory, antioxidant effects, hepatoprotective, and neuroprotective effects. Silybin exerts also pronounced effects on energy metabolism, that could be useful for sport horses. The aim of this study is to evaluate the effect of milk thistle seed cakes (in the form of a granulated mixture with barley) on blood biochemical parameters (total protein, albumin, bilirubin, urea, creatinine, ALT, AST, ALP, GGT, LDH, the total cholesterol, HDL-cholesterol, LDL-cholesterol, TAG, BHB, NEFA, creatine kinase, lactate, glucose, glutathione peroxidase, total antioxidant capacity, cortisol, calcium, and phosphorus) to monitor the differences between the experimental (milk thistle in feed) and control horses after exposure of the monitored horses to heavy physical exercise (combined driving) total number of horses was 12 Czech Warmblood breed horses. The digestibility of silymarin (and its individual flavonolignans) and basic nutrients are also monitored in this study. Statistically significant differences (P < .05) were found mainly in plasma cortisol and NEFA levels. The results of this study confirmed the results of our previous studies. These results suggest that the feeding of milk thistle seed cakes has a possible positive effect on horse health and energy metabolism.
- Klíčová slova
- Exercise, Horse nutrition, Plasma biochemical parameters, Silymarin, silybin,
- MeSH
- antioxidancia farmakologie MeSH
- biologické přípravky * metabolismus MeSH
- flavonoidy metabolismus MeSH
- hydrokortison metabolismus MeSH
- koně MeSH
- kyseliny mastné neesterifikované metabolismus MeSH
- ostropestřec mariánský metabolismus MeSH
- semena rostlinná metabolismus MeSH
- silymarin * farmakologie MeSH
- tělesná námaha MeSH
- zvířata MeSH
- Check Tag
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- antioxidancia MeSH
- biologické přípravky * MeSH
- flavonoidy MeSH
- hydrokortison MeSH
- kyseliny mastné neesterifikované MeSH
- silymarin * MeSH
Antibiotic resistance is currently a serious health problem. Since the discovery of new antibiotics no longer seems to be a sufficient tool in the fight against multidrug-resistant infections, adjuvant (combination) therapy is gaining in importance as well as reducing bacterial virulence. Silymarin is a complex of flavonoids and flavonolignans known for its broad spectrum of biological activities, including its ability to modulate drug resistance in cancer. This work aimed to test eleven, optically pure silymarin flavonolignans for their ability to reverse the multidrug resistance phenotype of Staphylococcus aureus and reduce its virulence. Silybin A, 2,3-dehydrosilybin B, and 2,3-dehydrosilybin AB completely reversed antibiotic resistance at concentrations of 20 µM or less. Both 2,3-dehydrosilybin B and AB decreased the antibiotic-induced gene expression of representative efflux pumps belonging to the major facilitator (MFS), multidrug and toxic compound extrusion (MATE), and ATP-binding cassette (ABC) families. 2,3-Dehydrosilybin B also inhibited ethidium bromide accumulation and efflux in a clinical isolate whose NorA and MdeA overproduction was induced by antibiotics. Most of the tested flavonolignans reduced cell-to-cell communication on a tetrahydrofuran-borate (autoinducer-2) basis, with isosilychristin leading the way followed by 2,3-dehydrosilybin A and AB, which halved communication at 10 µM. Anhydrosilychristin was the only compound that reduced communication based on acyl-homoserine lactone (autoinducer 1), with an IC50 of 4.8 µM. Except for isosilychristin and anhydrosilychristin, all of the flavonolignans inhibited S. aureus surface colonization, with 2,3-dehydrosilybin A being the most active (IC50 10.6 µM). In conclusion, the selected flavonolignans, particularly derivatives of 2,3-dehydrosilybin B, 2,3-dehydrosilybin AB, and silybin A are non-toxic modulators of S. aureus multidrug resistance and can decrease the virulence of the bacterium, which deserves further detailed research.
- Klíčová slova
- Efflux pump, Flavonolignans, Multidrug resistance, Silybin, Silychristin, Staphylococcus aureus,
- MeSH
- antibakteriální látky farmakologie MeSH
- antibiotická rezistence MeSH
- lidé MeSH
- silibinin farmakologie MeSH
- silymarin * chemie farmakologie MeSH
- stafylokokové infekce * MeSH
- Staphylococcus aureus MeSH
- virulence MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- Názvy látek
- antibakteriální látky MeSH
- silibinin MeSH
- silymarin * MeSH
